WO2008020469A1 - Composition de résine photosensible positive, procédé de préparation d'un motif et composant électronique - Google Patents

Composition de résine photosensible positive, procédé de préparation d'un motif et composant électronique Download PDF

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Publication number
WO2008020469A1
WO2008020469A1 PCT/JP2006/316018 JP2006316018W WO2008020469A1 WO 2008020469 A1 WO2008020469 A1 WO 2008020469A1 JP 2006316018 W JP2006316018 W JP 2006316018W WO 2008020469 A1 WO2008020469 A1 WO 2008020469A1
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Prior art keywords
group
photosensitive resin
resin composition
acid
positive photosensitive
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PCT/JP2006/316018
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English (en)
Japanese (ja)
Inventor
Hajime Nakano
Noriyuki Yamazaki
Yoshiko Futagawa
Yoshika Satou
Dai Kawasaki
Takumi Ueno
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Hitachi Chemical Dupont Microsystems, Ltd.
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Priority to JP2008529792A priority Critical patent/JPWO2008020469A1/ja
Priority to KR1020097002368A priority patent/KR101065146B1/ko
Priority to PCT/JP2006/316018 priority patent/WO2008020469A1/fr
Priority to US12/377,419 priority patent/US8097386B2/en
Publication of WO2008020469A1 publication Critical patent/WO2008020469A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/085—Photosensitive compositions characterised by adhesion-promoting non-macromolecular additives
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Definitions

  • the present invention relates to a positive photosensitive resin composition having heat resistance and a method for producing a relief pattern using the same.
  • the present invention also relates to an electronic component such as a semiconductor device having a surface protective film, an interlayer insulating film, and the like formed using the positive photosensitive resin composition.
  • Polyimide resin is excellent in heat resistance and has a property of being excellent in properties, so it is widely used in the field of semiconductor elements and the like.
  • polyimide resin is used as an interlayer insulating film or a surface protective film (buffer coat) provided between a sealing agent and a semiconductor chip.
  • the surface protective film means that the aluminum thin film circuit or the oxide film formed in the previous process is damaged during the work in the subsequent process, or after the semiconductor chip is mounted, the sealing material It is a film that prevents cracks from occurring due to the difference in thermal expansion coefficient between silicon and silicon.
  • the surface protective film made of polyimide resin not only protects the chip from external damage, but also has the ability to protect from radiation damage because of its high X-ray stopping power!
  • polyimide resin is also attracting attention as a tool for performing patterning force easily and reliably.
  • a photosensitive resin is imparted to a polyimide resin by a method in which a compound having a photosensitive group is added to or mixed with an acidic functional group of a polyimide precursor, and coating, exposure, and development are performed.
  • Photosensitive polyimides that can form relief patterns more easily are becoming mainstream (see, for example, Patent Documents 1 and 2).
  • the conventional polyimide-based resin is made of copper and copper, which are widely used as semiconductor materials.
  • metals such as copper alloys. This is because a chemical reaction occurs with metals such as carboxyl group copper and copper alloys, which are acidic functional groups contained in the structure of the polyamic acid of the polyimide precursor.
  • the polybenzoxazole precursor since the polybenzoxazole precursor has a phenolic hydroxyl group as an acidic functional group, it causes a corrosive action on copper or a copper alloy like the polyimide precursor, resulting in poor insulation.
  • Various problems such as disconnection, short circuit, flaws in metal parts, deterioration of film adhesion, and deterioration of film physical properties were caused.
  • Patent Document 1 Japanese Patent Laid-Open No. 54-109828
  • Patent Document 2 Japanese Patent Laid-Open No. 4-204945
  • Patent Document 3 Japanese Patent Publication No. 1-40862
  • Patent Document 4 JP-A-8-286374
  • the present invention has been made to solve the conventional problems as described above, and an object of the present invention is to prevent corrosion of copper and copper alloys such as metal wirings and metal layers. Dense An object of the present invention is to provide a positive photosensitive resin composition for an electronic material having a deposition effect, particularly a film adhesion effect under severe conditions such as heating and pressurization, and a method for producing a pattern and an electronic component. Another object of the present invention is to provide a photosensitive resin composition for electronic materials, a pattern production method, and an electronic component which have an effect of preventing a residual film in addition to the above effects and have a good sensitivity.
  • the positive photosensitive resin composition according to the present invention comprises (A) the following general formula (I)
  • X is a divalent organic group
  • Y is a tetravalent organic group
  • R is hydrogen or a monovalent organic group
  • m is 2 to
  • each of the polybenzoxazole precursors represented by (A) -general formula (I) has no reactive reactivity. It is characterized by having a! / Saturated bond, a reactive unsaturated bond, or an acyclic saturated bond.
  • the X and Y forces in the polybenzoxazole precursor represented by (A) -general formula (I) are 1 or 2 respectively.
  • the above cyclic aliphatic group or aromatic group, and the two or more cyclic aliphatic groups or aromatic groups are a single bond.
  • a group force consisting of an organic group or oxygen, sulfur, nitrogen, or silicon, and is bonded to each other by at least one heteroatom selected.
  • the compound (D) that generates an acid by light is an o-quinonediazide compound.
  • the positive photosensitive resin composition is applied on a support substrate and dried, and the photosensitive resin obtained by the application and drying is applied.
  • the electronic component according to the present invention is characterized by having a pattern layer obtained by the pattern manufacturing method.
  • the positive photosensitive resin composition of the present invention provides film adhesion without corroding copper and copper alloys such as metal wiring and metal layers, particularly film adhesion under severe conditions such as heating and pressing.
  • the effect and sensitivity are also good. In addition to the above effects, it has a residual film preventing effect, good sensitivity, and excellent reliability.
  • a pattern having a good shape with high resolution can be obtained by using the positive photosensitive resin composition.
  • the electronic component of the present invention has a relief pattern with a good shape, adhesion and heat resistance, and has an effect of high reliability.
  • FIG. 1 is a schematic cross-sectional view for explaining a manufacturing process of a semiconductor device having a multilayer wiring structure according to an embodiment of the present invention.
  • FIG. 2 is a schematic cross-sectional view illustrating a manufacturing process of a semiconductor device having a multilayer wiring structure according to an embodiment of the present invention.
  • FIG. 3 is a schematic cross-sectional view illustrating a manufacturing process of a semiconductor device having a multilayer wiring structure according to an embodiment of the present invention.
  • FIG. 4 shows the manufacture of a semiconductor device having a multilayer wiring structure according to an embodiment of the present invention It is a schematic sectional drawing explaining a process.
  • FIG. 5 is a schematic cross-sectional view illustrating a manufacturing process of a semiconductor device having a multilayer wiring structure according to an embodiment of the present invention.
  • the positive photosensitive resin composition of the present invention comprises (A) the following general formula (I)
  • X is a divalent organic group
  • Y is a tetravalent organic group
  • R is hydrogen or a monovalent organic group
  • m is 2 to
  • component (A) polybenzoxazole precursor
  • the precursor examples include a precursor that can be obtained by reacting a dicarboxylic acid and bisaminophenol. These polymers have an acidic functional group such as a phenolic hydroxyl group and Z or a derived substituent thereof in the structure.
  • the polybenzoxazole precursor has a structure represented by the general formula (I), because the good film characteristics can be obtained.
  • X is a divalent organic group
  • Y is a tetravalent organic group
  • R is hydrogen or a monovalent organic group
  • m is 2 to
  • X in the general formula (I) is a divalent organic group, and is an aliphatic group or an aromatic group having a linear, branched, or cyclic structure.
  • Examples of the aliphatic group include an alkyl chain, a cyclopentyl ring, a cyclohexyl ring, a cyclooctyl ring, and other bicyclo rings, and the aliphatic group may have a substituent.
  • the skeleton of these aliphatic groups may contain heteroatoms such as oxygen, sulfur, nitrogen and silicon or organic groups such as ketones, esters and amides.
  • ketone, ester, amide, alkylidene including those in which a hydrogen atom is replaced by a halogen atom such as a fluorine atom
  • Two or more aliphatic groups may be combined by, for example.
  • Examples of the aromatic group include a benzene ring and a naphthalene ring.
  • aromatic groups may have a substituent on the aromatic group, and the substituent may contain a hetero atom such as oxygen, sulfur, nitrogen and silicon.
  • a hetero atom such as oxygen, sulfur, nitrogen and silicon
  • single bonds or heteroatoms such as oxygen, sulfur, nitrogen and silicon or organic groups such as ketones, esters, amides, alkylide
  • Two or more aromatic rings may be bonded to each other by a hydrogen atom (including those in which a hydrogen atom is substituted with a halogen atom such as a fluorine atom).
  • Examples of the aliphatic dicarboxylic acid compound as the dicarboxylic acid compound having the organic group X include, for example, malonic acid, methylmalonic acid, dimethylmalonic acid, butylmalonic acid, succinic acid, glutaric acid, 2 , 2—Dimethyldaltaric acid, adipic acid, itaconic acid, maleic acid, tetrafluoromaleic acid, diglycolic acid, 1,1-cyclobutanedicarboxylic acid, 1,2-cyclopentanedicarboxylic acid, 3, 3— Tetramethylene glutaric acid, camphoric acid, 1,2 cyclohexanedicarboxylic acid, 1,3 cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 1,3 adamantanedicarboxylic acid, 5 norbornene 2, 3 Dicarboxylic acid, 1,2 phenylene diacetic acid, 1,3
  • aromatic dicarboxylic acid compounds include phthalic acid, 3-fluorophthalic acid, 4 fluorophthalic acid, 3, 4, 5, 6-tetrafluorophthalic acid, isophthalic acid, 2 fluoroisophthalic acid, 4 Fluoroisophthalic acid, 5 Fluoroisophthalic acid, 2, 4, 5, 6—Tetrafluoroisophthalic acid, terephthalic acid, 2, 2 bis (4 ruboxyphenol) propane, 2, 2 bis (4 , Carboxyphenyl) hexafluoropropane, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxydiphenyl sulfone, 4,4'-dicarboxydiphenylthioether, 4, 4 ' Dicarboxybenzophenone, 2, 2'-bis (trifluoromethyl) 4, 4'-biphenyldicaric acid, 2, 2'-bis (trifluoromethyl) 4, 4'-biphenyldicardicaric acid, 2, 2'-bis
  • Y in the general formula (I) is a tetravalent organic group, and is an aliphatic group or an aromatic group having a linear, branched, or cyclic structure.
  • the aliphatic group include an alkyl chain, a cyclopentyl ring, a cyclohexyl ring, a cyclooctyl ring, and other bicyclo rings, and the aliphatic group may have a substituent. In addition, they may contain heteroatoms such as oxygen, sulfur, nitrogen and silicon or organic groups such as ketones, esters and amides in the skeleton.
  • a single bond or a hetero atom or an organic group such as oxygen, sulfur, nitrogen, or silicon for example, a ketone, an ester, an amide or an alkylidene (including a hydrogen atom substituted by a halogen atom such as a fluorine atom) ) Etc., two or more aliphatic groups may be bonded.
  • Examples of the aromatic group include a benzene ring and a naphthalene ring.
  • substituents on the aromatic group may have a substituent on the aromatic group, and the substituent may contain a hetero atom such as oxygen, sulfur, nitrogen and silicon.
  • a single bond or a hetero atom or organic group such as oxygen, sulfur, nitrogen, silicon, etc., for example, ketone, ester, amide, alkylidene (including those in which a hydrogen atom is substituted by a halogen atom such as a fluorine atom)
  • Two or more aromatic rings may be bonded by, for example.
  • the organic group Y an aromatic group is preferable because of its heat resistance.
  • the bisaminophenol compound having the organic group Y is not particularly limited.
  • These bisaminophenols are used alone or in combination of two or more.
  • the polybenzoxazole precursor represented by the general formula (I) includes, for example, an active ester compound derived from a dicarboxylic acid having an organic group X with respect to a diamino compound having an organic group Y. It can be synthesized by reacting a product or an acid halide compound in an organic solvent. [0041] When the polybenzoxazole precursor represented by the general formula (I) is synthesized, the equivalent ratio of the dicarboxylic acid having the organic group X and the diamino compound having the organic group Y is defined as 0.6 ⁇ XZ Y ⁇ 1 5 is preferred. When the equivalent ratio of the dicarboxylic acid having an organic group X to the diamino compound having an organic group is outside the above range, the weight average molecular weight becomes small and the film properties are lowered.
  • both terminal portions of the obtained polybenzoxazole precursor can be made to be an amino group or a carboxyl group.
  • both ends of the polybenzoxazole precursor do not have various reactive unsaturated bonds! /, Cyclic bonds, reactivity It may be a group having an unsaturated bond or an acyclic saturated bond.
  • Hetero atoms or organic groups such as oxygen, sulfur, nitrogen, silicon, etc., including ketones, esters, amides, alkylidenes (including those in which a hydrogen atom is substituted by a halogen atom such as a fluorine atom) Including it!
  • Preferable functional groups for favorably controlling the solubility are those having 1 to 15 carbon atoms contained in the functional groups, for example, methyl group, ethyl group, propyl group, isopropyl group.
  • both terminal portions of the resulting polybenzoxazole precursor Becomes an amino group.
  • a photosensitive resin composition containing a compound that generates an acid by light (D) which will be described later
  • the amino group at the terminal portion is a primary amine
  • the stability of the photosensitive resin composition is reduced by a side reaction. Since at least one of the two hydrogen atoms on the amino group is substituted with another atom or other functional group in order to obtain stability as a photosensitive resin composition. I like it.
  • the substitution ratio is more preferably in the range of 30% to 100% in order to obtain sufficient stability.
  • R is a monovalent organic group having 1 to 20 carbon atoms
  • Z is an oxygen, sulfur or nitrogen atom, and Z is an oxygen atom or sulfur atom.
  • n l
  • n 2.
  • R for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group
  • R is an aliphatic group or an aromatic group having a linear, branched, or cyclic structure.
  • This structure can be obtained by reacting an amine with an acid anhydride having R. This acid anhydride
  • Succinic anhydride glutaric anhydride, 2,2-dimethyldaltaric anhydride, maleic anhydride, 1,2-cyclopentanedicarboxylic anhydride, 1,2-cyclohexanedicarboxylic anhydride,
  • Examples include norbornene-2,3 dicarboxylic anhydride, phthalic anhydride, 3-fluorophthalic anhydride, 4-fluorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride.
  • Examples of the aliphatic group for R include an alkyl chain, a cyclopentyl ring, a cyclo
  • aliphatic group may have a substituent. They are also heterogeneous such as oxygen, sulfur, nitrogen and silicon in the skeleton. And / or organic groups such as ketones, esters, amides, alkylidenes (including those in which a hydrogen atom is substituted by a halogen atom such as a fluorine atom), etc.
  • examples of the aromatic group in R include a benzene ring and a naphthalene ring.
  • I can get lost.
  • substituents on the aromatic group may contain a hetero atom such as oxygen, sulfur, nitrogen and silicon.
  • hetero atom such as oxygen, sulfur, nitrogen and silicon.
  • single bonds or hetero atoms or organic groups such as oxygen, sulfur, nitrogen, silicon, etc., for example, ketones, esters, amides, alkylidenes (including those in which hydrogen atoms are substituted by halogen atoms such as fluorine atoms), etc.
  • two or more aromatic rings may be bonded together.
  • R and R are classified according to the presence or absence of a reactive unsaturated bond (carbon-carbon unsaturated bond),
  • Examples of the group having a reactive unsaturated bond and having a cyclic structure include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexenyl group, and a norbornyl group.
  • a group derived from maleic anhydride which has an imide structure, which is shown second from the right in the general formula ( ⁇ ).
  • the cyclic structure does not have a reactive unsaturated bond, but has a group having a reactive unsaturated bond in addition to the cyclic structure, for example, a benzene ring and has a reactive unsaturated bond outside the benzene ring.
  • Groups with heavy bonds are also included in this category.
  • the group having a reactive unsaturated bond and having an acyclic structure is the structure shown on the right side of the general formula ( ⁇ ), which is derived from maleic anhydride. Group.
  • acid anhydride-derived groups such as acid anhydride, phthalic anhydride, 3-fluorophthalic anhydride, 4-fluorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride.
  • a group having no reactive unsaturated bond and an acyclic structure (acyclic saturated bond), a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, t-butyl group, trifluoromethyl group, methoxyethyl group, ethoxyethyl group, methoxymethyl group, ethoxymethyl group, methoxyethoxymethyl group, 2-trimethylsilylethoxymethyl group, trimethylsilyl group, t-butyldimethylsilyl group, the above general formula
  • the structure shown on the right side of ( ⁇ ) includes groups derived from succinic anhydride, glutaric anhydride, and 2,2-dimethyldaltaric anhydride.
  • the group having a reactive unsaturated bond or an acyclic saturated bond refers to the groups listed in the above (1), (2) and (4).
  • the above (3) is a cyclic bond having no reactive unsaturated bond, that is, a group having no cyclic unsaturated bond but no reactive unsaturated bond. No! /, A group with a cyclic bond (3) and an acyclic saturated bond (4) also favors stability points.
  • both end portions of the resulting polybenzoxazole precursor becomes a carboxyl group.
  • a carboxyl group it can be substituted with another functional group.
  • the terminal portion can be substituted by adding an amino compound during the synthesis of the polybenzoxazole precursor.
  • Examples of the amino compound include ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, t-butylamine, jetylamine, dipropylamine, diisopropylamine, dibutylamine, cyclopropylamine, cyclobutylamine, cyclopentyl, and the like.
  • Aliphatic amines such as amamine, cyclohexylamine, cyclohexylmethylamine, aniline, o toluidine, m-toluidine, p toluidine, o aromatic amines such as aminophenol, m-aminophenol, p-aminophenol Etc. Also, the present invention is not necessarily limited to those listed here.
  • the polybenzoxazole precursor represented by the general formula (I) has a molecular weight in the range of 5,000 to 80,000 in terms of weight average molecular weight. More preferably in the range of 40,000.
  • the weight average molecular weight can be determined by measuring with a gel permeation chromatography method and converting using a standard polystyrene calibration curve.
  • Examples of the solvent (B) in the present invention include ⁇ -petit-mouth ratatones, ⁇ -methyl 2-pyrrolidone, ⁇ acetyl-l-2-pyrrolidone, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylacetamide, Other polar solvents such as dimethyl sulfoxide, hexamethyl phosphortriamide, dimethylimidazolidinone, ⁇ acetyl- ⁇ -force prolatata are preferred, and in addition to these polar solvents, ketones, esters, ratatones, ethers, Halogenated hydrocarbons, hydrocarbons such as acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate, butyl acetate, dimethyl oxalate, jetyl malonate, jetyl ether,
  • organic solvents can be used alone or in combination of two or more. Used. However, the type is not particularly limited as long as it dissolves the photosensitive resin composition according to the present invention. Generally, the solvent is used in an amount of 40 to 90% by weight in the photosensitive resin composition.
  • component (C) examples include 1H-tetrazole, 5-methyl-1H-tetrazole, 5 phenyl 1H-tetrazole, 5 amino-1H-tetrazole, Examples thereof include 1-methyl-1H-tetrazole and 5,5′-bis-1H-tetrazole. Further, the present invention is not necessarily limited to those listed here.
  • components (C) are used alone or in combination of two or more.
  • the amount of component (C) used is usually 0.1 to 10 parts by weight per 100 parts by weight of component (A), 0.1 to 10 parts by weight in total when two or more are combined. It is. More preferably, it is in the range of 0.2 to 5 parts by weight. If the amount is less than 1 part by weight, the effect of improving the adhesion to the metal layer tends to be reduced. If the amount exceeds 10 parts by weight, no significant improvement in adhesion is expected even if it is added more.
  • component (D) a compound capable of generating an acid by light
  • component (D) is a photosensitizer and has a function of generating an acid and increasing the solubility of the light irradiation part in an alkaline aqueous solution.
  • component (D) used in the present invention any compound that generates an acid by light may be used. Specifically, for example, o-quinonediazide compound, allyldiazium salt, dialoljoe Examples thereof include Donium salt and triarylsulfo-um salt.
  • the o-quinonediazide compound can be obtained, for example, by subjecting o-quinonediazidesulfuryl chlorides to a hydroxy compound, an amino compound or the like in the presence of a dehydrochlorinating agent.
  • Examples of the o-quinonediazidosulfuryl chlorides include, for example, benzoquinone 1,2-diazide-4-sulfoluclide, naphthoquinone-1,2-diazide-5-sulfol chloride, naphthoquinone mono; L, 2 diazide 4 Sulfoyul chloride and the like can be mentioned.
  • a hydroxy compound is preferable from the viewpoint of photosensitive characteristics.
  • hydroxy compound examples include hydroquinone, resorcinol, pyrogallol, bisphenolanol A, bis (2-hydroxyphenol) methane, bis (4hydroxyphenol) methane, 2hydroxyphenol and 4'-hydroxyphenol.
  • examples of the above-mentioned allyldiazo-um salt, diarrhodonium salt, and triarylsulfo salt include, for example, benzene diazo-um p-toluenesulfonate, diphenol-donium 9,10.
  • components (D) are used alone or in combination of two or more.
  • the amount of component (D) used is usually 0.1 to 40 parts by weight per 100 parts by weight of component (A), and 0.1 to 40 parts by weight in total when two or more types are combined. is there. More preferably, it is in the range of 1 to 20 parts by weight. When the amount is less than 1 part by weight, the effect as a photosensitizer tends not to be sufficiently observed. When the amount exceeds 40 parts by weight, when the resin layer is exposed, the bottom is not sufficiently exposed.
  • a silane coupling agent can be used as an adhesion enhancer for the silicon substrate in the positive photosensitive resin composition of the present invention.
  • Y in the above general formula (I) derived from diaminosiloxane and modified to a base polymer can also be used as an adhesion enhancer for a silicon substrate.
  • a dissolution inhibitor, a stabilizer and the like may be added according to the purpose.
  • silane coupling agent reactive point alkoxysilanes are preferred.
  • a dissolution accelerator can be used for the purpose of increasing dissolution contrast.
  • the solubility promoter include a compound containing an acidic functional group.
  • the acidic functional group a phenolic hydroxyl group, a carboxyl group, and a sulfonyl group are preferable.
  • Such dissolution promoters include, for example, bis (2 hydroxyphenol) methane, bis (4 hydroxyphenol) methane, 2 hydroxyphenol mono 4'-hydroxyphenol methane, bis (2 hydroxysiloxane).
  • the photosensitive resin composition of the present invention is applied on a support substrate, which is a base material such as silicon wafer, metal substrate, ceramic substrate, etc. by dipping, spraying, screen printing, spin coating, etc. To do.
  • a support substrate which is a base material such as silicon wafer, metal substrate, ceramic substrate, etc.
  • the resulting photosensitive resin coating is appropriately heated and dried.
  • a photoresist is applied onto the photosensitive resin coating, and an exposure process is performed in which actinic rays or actinic rays are irradiated through a mask on which a desired pattern is drawn.
  • a contact Z proximity exposure machine using an ultrahigh pressure mercury lamp, a mirror projection exposure machine, an i-line stepper, a g-line stepper, other ultraviolet rays, a visible light source, an X-ray, An electron beam can be used.
  • PEB post-exposure heating
  • a desired positive pattern can be obtained by dissolving and removing the exposed portion with a developer.
  • an alkaline aqueous solution is used.
  • an aqueous solution of alkali metal hydroxide such as caustic potash or caustic soda, tetrahydroxide ammonium hydroxide, tetraethyl ammonium hydroxide, choline hydroxide or the like.
  • Amine aqueous solutions such as grade ammonia, ethanolamine, propylamine, and ethylenediamine are used.
  • the rinsing liquid for example, methanol, ethanol, isopropyl alcohol, benzene, toluene, xylene, methyl mouth sorb, water, or the like is used. Thereafter, by removing the photoresist and heating the resulting pattern, the solvent or the solvent and the photosensitizer can be removed to obtain a stable high heat resistant polybenzoxazole pattern.
  • the heating temperature is preferably 150 to 500 ° C, more preferably 200 to 400 ° C, more preferably force S. This is because if the heating temperature is less than 150 ° C, the mechanical and thermal properties of the film tend to deteriorate, and if it exceeds 500 ° C, the mechanical and thermal properties of the film tend to deteriorate. .
  • the heating time is preferably 0.05 to 10 hours. This is because if the heating time is less than 0.05 hours, the mechanical and thermal properties of the film tend to deteriorate, and if it exceeds 10 hours, the mechanical and thermal properties of the film tend to deteriorate. .
  • the positive photosensitive resin composition and pattern manufacturing method of the present invention can be used for electronic components such as semiconductor devices and multilayer wiring boards.
  • the surface protection of semiconductor devices can be used. It can be used for forming a protective film layer, an interlayer insulating film layer, an interlayer insulating film layer of a multilayer wiring board, and the like.
  • the electronic component of the present invention is not particularly limited except that it has a surface protective film layer and a Z or interlayer insulating film layer formed using the positive photosensitive resin composition, and has various structures. Can do.
  • Electronic components include semiconductor devices, multilayer wiring boards, various electronic devices, and the like.
  • 1 to 5 are schematic cross-sectional views for explaining a manufacturing process diagram of a semiconductor device having a multilayer wiring structure. A series of steps from the first process to the fifth process are respectively performed from FIG. 1 to FIG. Represents the degree.
  • a semiconductor substrate 1 such as a Si substrate having a circuit element (not shown) is covered with a protective film 2 such as a silicon oxide film except for a predetermined portion of the circuit element, and exposed.
  • a first conductor layer 3 is formed on the circuit element.
  • An interlayer insulating film layer 4 is formed on the semiconductor substrate 1 by a spin coat method or the like (first step, FIG. 1).
  • a photosensitive resin layer 5 such as a salty rubber system or phenol novolac system is formed on the interlayer insulating film layer 4 as a mask by a spin coating method, and a known photolithography technique (photolithodar)
  • a window 6A is provided so that a predetermined portion of the interlayer insulating film layer 4 is exposed (second step, FIG. 2).
  • the interlayer insulating film layer 4 exposed from the window 6A is selectively etched by dry etching means using a gas such as oxygen or carbon tetrafluoride so that the window 6B is opened.
  • the photosensitive resin layer 5 is completely removed by using an etching solution that only corrodes the photosensitive resin layer 5 that does not corrode the first conductor layer 3 exposed from the window 6B (first resin layer 5). Figure 3).
  • the second conductor layer 7 is formed using a known photolithography technique, and the electrical connection with the first conductor layer 3 is completely performed (fourth step, Fig. 4).
  • each layer can be formed by repeating the above steps.
  • the surface protective film layer 8 is formed.
  • the photosensitive resin composition is applied and dried by a spin coating method, and a pattern on which a window 6C is formed in a predetermined portion is drawn. Develop with to form a pattern and heat
  • the surface protective film layer 8 is formed (fifth step, FIG. 5).
  • This surface protective film layer 8 protects the conductor layer with a force such as stress from the outside and ⁇ rays, and the obtained semiconductor device is excellent in reliability.
  • the interlayer insulating film layer 4 can also be formed using the positive photosensitive resin composition of the present invention.
  • the precipitated solid was further washed with ion-exchanged water, sucked and dried on a filtration filter, and further dried under reduced pressure to obtain polymer P-1.
  • the water content of this polymer was 0.8% by weight, the weight average molecular weight was 22,800, and the degree of dispersion was 1.8.
  • the solution was cooled to 0 ° C., and the reaction solution A-5 obtained earlier was added dropwise over 30 minutes, followed by stirring at room temperature for 30 minutes.
  • the reaction mixture was treated with 2.01 ion exchange water with vigorous stirring.
  • the precipitated solid was further washed with ion-exchanged water, sucked and dried on a filtration filter, and further dried under reduced pressure to obtain polymer P-6.
  • the polymer had a water content of 0.7% by weight, a weight average molecular weight of 23,000, and a degree of dispersion of 1.7.
  • This positive photosensitive resin composition solution was formed by sputtering a TiN film with a film thickness of about 200A on a 5-inch silicon substrate, and a Cu film with a film thickness of about 5000A sputtered on it ( (Hereinafter referred to as “Cu Ueno”) After spin coating on the substrate and drying by heating to form a coating film of 10., the exposure dose was set to 700 mjZcm 2 using an i-line stepper and exposed through a mask. . When this was paddle developed with a 2.38% tetramethylammonium hydroxide aqueous solution, a good relief pattern was obtained. Furthermore, it was heated in an oven purged with nitrogen at 300 ° C. for 1 hour to obtain a cured film having a thickness of 7 ⁇ m.
  • a stud pull test was performed as an adhesion test using the obtained cured film on the wafer.
  • model number 901106 (2.7 mm) of a stud pin (A1 with epoxy adhesive) manufactured by Phototech Co., Ltd. was used.
  • Adhesion between the stud pin and the cured film was performed by curing with an oven at 150 ° C for 1 hour. As a result, it showed an adhesive force of 68.6 MPa and sufficient adhesion to the Cu film.
  • a wafer that has been cured is treated at 121 ° CZ0.20 MPa for 100 hours using a pressure tacker (hereinafter referred to as “after PCT treatment”), and then a stud pull test is performed. It was. As a result, it showed an adhesive strength of 66.7 MPa, and the adhesion to the Cu film did not deteriorate even after PCT treatment.
  • Example 3 The same composition as in Example 1 except that polymer P-2 was used instead of polymer P-1, and ureidopropyltriethoxysilane was used instead of bis (2-hydroxyethyl) -3-aminopropyltriethoxysilane.
  • a positive photosensitive resin composition solution was prepared. This positive-type photosensitive resin composition solution was processed and tested in the same manner as in Example 1 except that the exposure dose was 800 miZcm 2 . As a result, a good relief pattern was obtained with an exposure dose of 800 mj / cm 2 .
  • the stud pull test of the cured film obtained by carrying out the same process as Example 1 was conducted. As a result, it showed an adhesive strength of 66.7 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 64.7 MPa after PCT treatment, and the adhesion to the Cu film was almost intact after PCT treatment. [0097]
  • Example 3 Example 3
  • P—3 is replaced with 2- (4 hydroxyphenyl) 2- (4- [1,1-bis (4-hydroxyphenyl) ethyl] phenyl] propane and naphthoquinone 1, Compound prepared by reacting 2diazido 5-sulfochloride with a molar ratio of 1Z2.5. 1. Instead of 50g, tris (4-hydroxyphenyl) methane and naphthoquinone 1,2diazide 5sulfodichloride 1Z2. A positive photosensitive resin composition solution having the same composition as in Example 1 was prepared except that compound 1. Og reacted at a molar ratio of 8 was used.
  • This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1 except that the exposure dose was 500 miZcm 2 . As a result, a good relief pattern was obtained with an exposure dose of 500 mi / cm 2 . Moreover, the stud pull test of the cured film obtained by performing the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 70.6 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 67.7 MPa after PCT treatment, and the adhesion to the Cu film hardly deteriorated after PCT treatment.
  • Polymer P—4 instead of polymer P—1, Naphthoquinone 1,2 diazido 4-sulfonyl chloride instead of naphthoquinone 1,2 diazido 5-sulphonyl chloride, bis (2 hydroxyethyl) 3 aminopropyltriethoxy
  • a positive photosensitive resin composition solution was prepared with the same composition as in Example 1 except that ureido-opened pyrtriethoxysilane was used instead of silane.
  • This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1. As a result, a good relief pattern was obtained with an exposure amount of 700 mjZcm 2 .
  • Example 2 the stud pull test of the cured film obtained by carrying out the same process as Example 1 was conducted. As a result, it showed an adhesive strength of 65.7 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 66.7 MPa after PCT treatment, and the adhesion to the Cu film was almost intact after PCT treatment.
  • Example 3 A positive photosensitive resin composition solution was prepared with the same composition. This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1. As a result, a good relief pattern was obtained with an exposure dose of 700 mjZcm 2 .
  • Example 2 a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 62.8 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 64.7 MPa after PCT treatment, and the adhesion to the Cu film was almost unchanged after PCT treatment.
  • a positive photosensitive resin composition solution was prepared with the same yarn composition as in Example 5 except that polymer P-6 was used instead of polymer P-5.
  • This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1. As a result, a good relief pattern was obtained with an exposure dose of 700 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive force of 63.7 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 64.7 MPa after PCT treatment, and the adhesion to the Cu film was almost unchanged even after PCT treatment.
  • a positive photosensitive resin composition solution was prepared with the same composition as in Example 1 except that polymer P-7 was used instead of polymer P-1.
  • This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1. As a result, a good relief pattern was obtained with an exposure dose of 700 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 62.8 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 63.7 MPa after PCT treatment, and its adhesion to the Cu film remained almost unchanged after PCT treatment.
  • Example 2 When a test was conducted in the same manner as in Example 1 except that 1H-tetrazole was not added, a good relief pattern was obtained at an exposure amount of 700 mjZcm 2 . In addition, a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, 66.7 MPa The adhesion to the Cu film was sufficient. In addition, after PCT treatment, it showed an adhesive strength of 9.81 MPa, and the adhesive strength was reduced by PCT treatment.
  • Example 2 When a test was conducted in the same manner as in Example 2 except that 1H-tetrazole was not added, a good relief pattern was obtained at an exposure amount of 800 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive force of 65.7 MPa and sufficient adhesion to the Cu film.
  • PCT treatment After PCT treatment, it showed an adhesive strength of 12.7 MPa, and the adhesive strength was reduced by PCT treatment.
  • Example 3 When a test was conducted in the same manner as in Example 3 except that 1H-tetrazole was not blended, a good relief pattern was obtained at an exposure amount of 500 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 66.7 MPa and sufficient adhesion to the Cu film. In addition, after PCT treatment, it showed 6.86 MPa adhesive strength, and the PCT treatment decreased the adhesive strength.
  • Example 4 When a test was conducted in the same manner as in Example 4 except that 1H-tetrazole was not added, a good relief pattern was obtained at an exposure amount of 700 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 64.7 MPa and sufficient adhesion to the Cu film. Moreover, after PCT treatment, it showed an adhesive strength of 10.8 MPa, and the adhesive strength was reduced by PCT treatment.
  • Example 6 When a test was conducted in the same manner as in Example 6 except that 1H-tetrazole was not blended, a good relief pattern was obtained at an exposure amount of 700 mjZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, the adhesive strength of 62.8MPa was shown and the adhesion to the Cu film was sufficient. Moreover, after PCT treatment, it showed an adhesive strength of 14.7 MPa, and the adhesive strength was reduced by the PCT treatment.
  • a positive photosensitive resin composition solution was prepared in the same composition as in Example 1 except that benzotriazole was used instead of 1H-tetrazole.
  • This positive photosensitive resin composition solution was processed and tested in the same manner as in Example 1. As a result, a good relief pattern was obtained with an exposure dose of 700 miZcm 2 .
  • a stud pull test of a cured film obtained by the same treatment as in Example 1 was performed. As a result, it showed an adhesive strength of 66.7 MPa and sufficient adhesion to the Cu film. In addition, it showed an adhesive strength of 1.96 MPa after PCT treatment, and the adhesive strength was reduced by PCT treatment.
  • Table 1 summarizes the combinations of the polymers and nitrogen-containing heterocyclic compounds in Examples 1 to 7 and Comparative Examples 1 to 8, and the adhesion results.
  • the photosensitive resin composition of the present invention is excellent in heat resistance, adhesion, particularly film adhesion under severe conditions such as heating and pressurization, sensitivity, resolution, and residual film preventing effect. A relief pattern with a simple shape can be obtained. Therefore, the photosensitive resin composition of the present invention is excellent in reliability and is particularly suitable for the production of electronic parts.

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Abstract

La présente invention concerne une composition de résine photosensible positive pour matériau électronique qui ne provoquerait aucune réaction de corrosion du cuivre ou des alliages de cuivre du circuit métallique, entre autres, et dont l'adhérence de pellicule et la sensibilité sont excellentes ; et un procédé adapté de préparation de motif et un composant électronique. L'invention concerne une composition de résine photosensible positive comprenant un précurseur de polybenzoxazole (A) avec l'une quelconque des structures de formule générale : (I) (X est un groupe organique divalent ; Y un groupe organique tétravalent ; R1 l'hydrogène ou un groupe organique monovalent ; m un entier compris entre 2 et 500, représentant le nombre d'unités répétées du polymère), un solvant (B), un dérivé du tétrazole (C) et un composé (D) capable de générer de l'acide par exposition à la lumière.
PCT/JP2006/316018 2006-08-14 2006-08-14 Composition de résine photosensible positive, procédé de préparation d'un motif et composant électronique WO2008020469A1 (fr)

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KR1020097002368A KR101065146B1 (ko) 2006-08-14 2006-08-14 포지티브형 감광성 수지 조성물, 패턴의 제조방법 및 전자부품
PCT/JP2006/316018 WO2008020469A1 (fr) 2006-08-14 2006-08-14 Composition de résine photosensible positive, procédé de préparation d'un motif et composant électronique
US12/377,419 US8097386B2 (en) 2006-08-14 2006-08-14 Positive-type photosensitive resin composition, method for producing patterns, and electronic parts

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JP2009128550A (ja) * 2007-11-22 2009-06-11 Sumitomo Bakelite Co Ltd ポリアミド樹脂、ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置
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JP2014191252A (ja) * 2013-03-28 2014-10-06 Sumitomo Bakelite Co Ltd 感光性樹脂組成物、硬化膜、保護膜、半導体装置および表示体装置
US9482943B2 (en) 2013-08-13 2016-11-01 Cheil Industries Inc. Positive photosensitive resin composition, and photosensitive resin film and display device prepared by using the same

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US9410055B2 (en) * 2011-04-08 2016-08-09 Mitsubishi Gas Chemical Company, Inc. Polybenzoxazole resin and precursor thereof
KR102074200B1 (ko) * 2018-05-02 2020-03-02 송기용 저온경화 가능한 유기절연체 조성물 및 이를 이용한 유기절연막 제조방법

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JP2009080443A (ja) * 2007-09-06 2009-04-16 Sumitomo Bakelite Co Ltd ポリアミド樹脂、ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置
JP2009128550A (ja) * 2007-11-22 2009-06-11 Sumitomo Bakelite Co Ltd ポリアミド樹脂、ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置
JP2014191252A (ja) * 2013-03-28 2014-10-06 Sumitomo Bakelite Co Ltd 感光性樹脂組成物、硬化膜、保護膜、半導体装置および表示体装置
US9482943B2 (en) 2013-08-13 2016-11-01 Cheil Industries Inc. Positive photosensitive resin composition, and photosensitive resin film and display device prepared by using the same
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